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From Whitewater Rafting to CTO: Brian’s Path to Tech

In this episode, I sit down with Brian Childress, whose journey into software engineering took a completely unconventional path -- from guiding whitewater rafting trips to becoming a fractional CTO. We dive into how curiosity, resilience, and a willingness to learn can reshape a career, even without a traditional computer science background. Brian opens up about battling imposter syndrome, putting in the early mornings and late nights to self-teach coding, and how that drive eventually led him to help startups scale their platforms and teams. We also dig into what it really takes to grow from individual contributor to senior and tech lead, and how AI is changing expectations at every career level. Whether you’re just breaking into tech or figuring out how to lead others, this conversation is full of real, hard-earned lessons about perseverance, learning, and embracing discomfort as the price of growth.
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In this video interview, I sat down with Brian Childress. So, we went through his career journey, what it was like for him to experience imposter syndrome as well as a conversation around building up the different skills required when you're working as an IC working towards a senior or tech lead position. Towards the end of our conversation, we got into discussions around AI and what that means for different people at different stages of their career and the uncertainty that that brings. So, I think that you're really going to enjoy this one. There's a lot of interesting things to take away. So sit back, enjoy, and I'll see you in the next one. >> Brian, thank you for joining. Um, I guess to kick things off, if you don't mind giving us a bit of a career journey and like I mentioned before we started recording as early or as late as you want and kind of give people some background for who you are and how you got here. >> Yeah. Um, I I appreciate the opportunity to chat, Nick. Um, so my career path was not a straight uh or smooth one by any means. Um, I was not the kid at 8 years old like programming computer games on my like we didn't get a computer in the house until uh I was in high school. Uh, I kind of learned to type by uh, you know, AOL instant messenger. Um, you know, the dialup days. Um, that's how I really started to learn to type, but I didn't really have a passion for computers. Um, and so in undergrad, I actually um took the advice of follow your passion and got into uh outdoor recreation. So I spent several years guiding um across the US uh whitewater rafting and rock climbing and skiing. >> Awesome. >> Um super fun, man. Amazing. Um >> had a blast. uh realized that that was really fun, but it wasn't getting me to some of my bigger kind of goals and dreams. And so somewhere in there, I decided to go back to graduate school and got into geographic information systems. So that kind of aligned with um you know, some of my other passions, but you know, it wasn't like super computer, you know, scienceheavy. Uh so went back to school for that. Um and in that time really found a passion for uh for developing. So we were using a ton of Python to you know deal with these huge data sets and um in that time I was like man I I actually really like this. This is kind of scratching that intellectual itch that I was always looking for. Um and so just kind of you know finished up grad school and then um landed a job uh as a a government contractor building some software platforms um you know in various different uh arenas in healthcare and in finance. Um, interesting. So, it was not specifically related to like what you had gone to school for for like the th those systems and it happened to be a little bit more uh general. >> Uh, it so I did spend about four months kind of using uh all my graduate work. Okay. >> Um, and then just got into more just broad kind of software engineering. Um so yeah like you know the two years or whatever I had spent in graduate school I you know invested four months into the job force and then found like I I like some of these other pieces of it like the building components and not just you know the deep data analysis stuff. Um and so then I I just continued to get into uh just more software engineering type of things. Um, but really I I still don't have like a formal software engineering type of pedigree. I don't have that background. Um, and for me that led to just a boatload of imposttor syndrome as I'm coming into this. You know, I I I prided myself on not being the the guy that, you know, could restart a computer and build it from scratch. Like that wasn't me. Um, and now it was me and I needed to become that person. Uh, and so for me, I really, uh, I spent a ton of time, uh, you know, on the job, doing it, doing the best I could, learning, and and just soaking up from everyone around me. Uh, anyone that would teach me, I would, you know, uh, seek them out. Um, but what I found was I needed to dig in more. And so I was waking up at, you know, 5:00 a.m. and spending those first few hours before like official work started teaching myself, you know, everything from server architectures to WordPress websites and PHP and who knows what. Just every tutorial, everything that I could do to uh try and learn more and more. Uh and I would do the same in the evenings. And at that period of life, I was fortunate to be in a very strong startup ecosystem. So I uh I was going to like a meetup type of user group three or four nights a week. Uh surrounding myself with people that are also building, you know, um different systems and and just surrounding myself in all of this technology. Uh, so, you know, I like to think that, you know, while I've got a couple decades in the industry, like I I I added on quite a few more just in that time that I spent outside of, you know, the 9 to5 type of work. >> Um, continued to progress, uh, you know, I've worked in, uh, you know, consumer startups, um, large enterprises. Uh I like to say that I really focus on building and scaling systems and I do that through taking a just a very simple approach to it. Um and it's taken me quite a while to get to that place where now um I work with a few different companies as a fractional CTO. So I get to come in kind of after the platform is built um and help to grow the team, help to scale the platform, you know, stabilize and and do all of those things that a lot of organizations uh tend to need. >> Awesome. I have yeah a bunch of questions because it's super cool. I love the um you know the the journey going from I guess like as you said like you you didn't grow up being like definitely tech like I know I'm doing that and then kind of having this transition into it. So, you did mention imposter syndrome and that was like one of the first things I wanted to see if we could talk a little bit more about because it's just such a common thing and at the same time uh such a stigma around it where you know for people that you know haven't heard of it but they're definitely going through it. It's kind of this experience where you're like oh my god like I'm the only person like this. I must be stupid. I must not be worthy. And uh at least in my experience, I found the more that people talk about it, the more that you it doesn't like fix it, but it makes you realize like, hey, I'm not alone going through this and this is like a normal thing to experience. So for yourself, like was that a barrier getting into it? Like did you find that that started even before you started taking the first steps to kind of get into tech that that was preventative for you or did that start to kick in once you took those first steps and had your foot in the door? >> I I do think it kind of held me back. Uh I remember taking maybe visual basic and high school. Um and I I think I just I didn't I wasn't a good high school student. Uh I just wasn't. Um, and so like the logic makes sense uh to me now. Uh, I just I didn't put in the time. So I was like, "Oh, I'm just I'm not good at computers. I'm not going to be the computer guy. Uh, I don't want to spend 12 hours a day sitting behind a screen. I don't want to do that. Uh, now, you know, I spend 14 hours a day. Um, so, you know, it's I think that did kind of plant the seed of that's not for me." Um, and so I had to work past that and had to work past, you know, just not having that formal computer science deep understanding of the kernel and, you know, operating systems and all of these things. Um, but I found that my desire to learn uh helped get me past a lot of that. But I I don't know, imposttor syndrome doesn't go away. uh at least for me, everyone I've talked to, it doesn't go away. We just we learn to deal with it better or recognize when it's cropping up and just kind of push through it, you know? So, >> yeah, that's been yeah, similar experience for me and and folks I've talked to. It's uh when imposter syndrome seems to go away, it's it's usually because it's starting like somewhere else in like where you're growing, right? So you might experience it and then over time as you're getting more comfortable and confident as it's kind of waning it starts to pick up somewhere else where you're like having new challenges and start to go wait a second am I actually you know cut out for this but yeah that's uh that's awesome. Thank you for sharing that. Um the the point that you called out around like you know your your curiosity and wanting to learn. The other thing as you were talking that really stood out because I think and I I this is a generalization for sure, but I think that a lot of people I I hear from at least or I I see and like read about whether it's on social media or whatnot, there's this this feeling that like I want to get into tech and like get it's kind of I feel like human nature to be like what is the shortcut? Like what is the shortest path that I can condense into this? You guys must know it, right? Like you're in tech. like just give me the the cheat code. I want the three weeks. I want, you know, maybe maybe two months and like I want to be in tech and I want this salary and I feel like it's not um it's not realistic and unfortunately but >> what you called out was that you were putting in so much time to learn and um I'm just curious like >> did did that did you know like I I have to do this or was that more of like I need like that's helping my imposttor syndrome or like what was the what kept you driven to to be putting in that much time to for learning. >> Uh I I think I got to a point where I really did enjoy it, you know, like >> okay, >> you know, the the problems I think I I recognized that those were the things that I was missing in, you know, other interest areas, other career paths I had followed. Um was the problemolving aspect and I just I've always enjoyed learning. And I think because I didn't feel like I was a really good high school student, um, you know, that it was learning wasn't for me. It's like, no, that format, that approach. So, I had to try different ways and, you know, being very hands-on and building I found was something I really really enjoyed. Um, and, you know, I can spin up servers and I can do all of these things. Um, yeah, I and I would I would agree like most people do want that shortcut, right? The the coding boot camps of six weeks to six figure salary or you know, whatever their claim to fame is. Um, and across all of my teams, I continue to uh remind them it's like there are certain things that all of us have to just go through, right? All of us have to drop the production database. Like it just it's a you know, it's just it's on your journey. if you haven't done it yet, you're going to do it. And you know, let's just kind of prepare ourselves mentally for it. Um, and there's just things that have to happen. Uh, and all of our journeys look different. Uh, but we experience a lot of the same things. Uh, and imposter syndrome is definitely one of those. So, >> awesome. Yeah. The Sorry, there's one more question I wanted to ask you on on that and it's now escaping me. of course the uh the thing that I was thinking through was so on on the learning topics the it's cool that you sort of got to this point where you're like I I enjoy learning and I I know for myself it's like I like the the concept of it but I think that in practice I'm almost I don't want to say like afraid but uh I don't like the feeling of being a newbie um going from something where I feel like very skilled at it, very experienced, and someone's like, "Okay, like you're going to go do this thing." And I'm like, "I why do I have to do that thing because I I'm good at this, right?" Like, so I think I hold myself back a lot. And I'm curious, did you find that you were just able to like lean into like comfortable being uncomfortable sort of thing? >> Uh, not immediately. I mean, it took a good seven, eight, 10 years to really lean into it and recognize the fact that >> um because I was kind of holding back. It's like I'm an expert over here, you know, and I I'm not familiar with this, so I'm not going to venture into that area. That was holding me back. I wasn't growing anymore because after a while, like there's only so much more I can learn in this space, but there's other areas where I can learn and I can grow. Um, and you know, it really what I found is there's a been a very strong correlation between my background as like an outdoor uh guide and my work in technology, right? So, >> I I'm used to doing like pushing myself into uncomfortable areas, right? where I'm 100 or off the ground on some, you know, flat rock face like that is, you know, I have to work through that mental barrier of I I need to keep going. I need to get to the top. Um, you know, or or take some path there and that's that's a scary thing. That is physically scary. Um, and how does that align with, you know, some of the the similar feelings where I might restrict myself or hold myself back? Um but yeah, it's certainly not something I did immediately. It took quite a while to to come to. >> Yeah. Well, yeah, thanks for sharing that because I find like when I reflect for myself, that's one of the things I'm like I have to keep reminding myself that anytime it's happened, at least in my journey so far, you know, I'm putting to something that feels uncomfortable because I don't know it. And every single time it's like nothing bad happens. It's uncomfortable for a bit, but that's like learning and growth. And then over time it depends on how different the environment is but you know could be a couple months could be a year two years but gets to the point where it's like wait a second like no like I I do know this space like I've been working in this space I'm comfortable in this space um the imposttor syndrome part like does it completely go away no but like now I you know you build confidence along the way but I do have to remind myself for example if someone came to me knocked on my door right now and here's an opportunity. It's a interesting opportunity. You've never done anything like this before. >> Naturally, I would be like, "No." >> Like, I'm It's too scary. It's too uncertain. And I think I need to personally lean into more of that kind of thing because every single time it's happened in my life so far, it's been a lot of growth and a lot of experience. So, um it was interesting to hear you say that. It's not something where like, oh, you stuck with it for a couple weeks and all of a sudden it was like, yeah, I can lean into all this uncertainty. It takes like years to kind of build that up. >> Yeah. No, absolutely. Um, and I think I like that reflecting backwards and seeing um like that's a a big question I ask you a lot of friends if they're struggling with something. It's like, when was the last time that you failed at something, you know, that looked very similar? It's like, well, never. I I I put my all into it like well how is this new situation any different than what you've done before right it you know certain aspects are going to be different but your attitude your approach is going to be you know the same you haven't changed in that way and there's just another opportunity to grow >> yeah that's uh I think it's a really great way to look at it right is like you're you're going to be pushing through you're going to be learning and uh as I said when I reflect there hasn't been a time where I'm like I was put into something and it was catastrophic or something. There's times where things have been slower for sure. There's times where I surprise myself, but every single time there's been growth and sort of a positive outcome from that. So, uh, that's cool. Um, I guess I'm curious. I'm looking at sort of some of the notes that you sent over ahead of time. I wanted to hear your thoughts on like one of the notes you have here is going from an individual contributor into sort of more of like a senior type role or uh more of like a like a tech lead or team lead type of role. Um what does from your perspective what are sort of the elements that go into that for an individual like um where like how do they start on that that progression? Yeah, I think there's opportunities to lead um all throughout our career. It doesn't matter what our title is. We don't have to have a certain title in order to be a leader. Um you know, and I have the opportunity to coach and mentor like one-on-one or in groups a number of different folks that are like senior or tech lead or uh you know, I want to be a CTO one day. And in that the the biggest challenges that we work through is um really it's the shift away from their comfort zone right which is for many of us is the technology right I can I know if it compiles I know if I can see the thing on the screen or get the data that I want now I have to start and you know work with a completely different system which is other fleshy humans how do I work with >> oh no them right like they're way more unpredictable. Um, and so that's a completely different skill set and a shift. And you know, kind of like what we were talking about earlier, I think most people will step back into where they're comfortable uh into that into the technology. I'm just going to go and put my head down and, you know, crank through some, >> you know, user stories. Um, and that's that's a big shift. And so my recommendation to many people if they want to continue to grow in their career is to try and find ways to lead in certain areas, right? Lead a a feature, lead a start to lead a project. Um, you know, look for ways that they can bring in new technologies or ideas into the organization that they're working with. Um, that was one big one for me that I found was by doing a ton of side projects and, you know, small freelancing work, I was able to bring things that I was learning outside into the organization like, hey, why don't we try this? Why don't we, you know, and not just here's new shiny objects, but here's a new way that we can approach this problem. Um, and we can do that no matter what our title is. >> Yeah. Yeah. And that's a I think that's a really interesting example because the I like that you called out that it's not necessarily just hey it's shiny so we we must do it but that conversation ends up becoming like I'm trying to think through this if if I'm someone watching or listening to this and it's like okay so is the is the advice just go look at different tech and say bring it to the team and say we got to do this like no but that's that's the stepping stone right like the part the the skill set that you need to be able to build on top of that is if this is um something that you're thinking is valuable, you're like, "Hey, we should consider this." How do you convince other people about that? How do you have that conversation? How do you bring it up? How do you say to a group of people, "This is an idea I have. Here is why I think it's valuable. Here is evidence behind that. What are your thoughts?" Like, you know, those those steps are all really going to be um it's kind of weird to say, but like kind of like selling. you're gonna have like these personal, you know, interactions where you might be working with other people who also don't have a lot of experience trying to go back and forth like this and, you know, you're you need to work on this other set of skills. It's not just code or not just purely tech. Um, any any thoughts on sort of like the the specific people skills that come in on top of that? Yeah, it's uh the one thing I like to tell my teams is it's it's not about you. It's about understanding the person that you're talking to. What are their goals? What are the things that they need? Right? Do they uh want to make sure that the system grows? Do they want to, you know, reach their next promotion level? Like what are their interests? So that whatever it is that you think is going to help the organization overall, the new technology or or new approach or new architecture like how does that thing that I think is really good and I want to bring in how does that address their needs, their desires um because I can say man dude let's look at the you know the the requests per second that this particular architecture can have or you know this is why we need to go to a NoSQL database whatever it is like that's not that's that's the new shiny. That's the thing that you want and you think will solve the problem. >> Understanding the problem uh from someone else's perspective, I think is the really valuable piece. Um and we all hear information differently and in different ways. So, you know, maybe you and I can have a fantastic conversation, but somebody else needs to see it like in documentation and full written form and like a a detailed presentation. whatever it is like understand how they absorb and digest that information uh is also really important too. >> Yeah, that's a I think a really important factor. So, not only do we have this idea that different people are going to, you know, have different values or things that they're going to want out of a proposal, but the format in terms of how information is transferred is also incredibly valuable. Like I know for myself, just as an example, if someone were to like if I'm working remotely and someone's like, "Hey, like like I'm going to call you right now to talk about something and I if I haven't had time to prep or I don't have data upfront for me, that's very uncomfortable. So, it's not that it's wrong or that person should feel bad for doing it. But in terms of me being effective in whatever conversation they want to have, if I haven't had time to kind of think through it, then I I feel like I'm not going to be valuable to them cuz they might and you know, it might just be that they have a question that they think I can answer. And it's great if I can, but I feel uncomfortable if I don't have time to prep. So, I like things written. I like notes ahead of time. Um, I like data points, right? like I like being able to go digest actual like written information. So that's valuable for me. But yeah, the other entire part of that is like the reason I said selling is because I feel like selling is a good example of I mean number one it feels a little bit awkward to say selling when we're talking about like software development. It's like oh that's that's an uncomfortable thing. But with selling it's really about understanding your target audience, right? Like why would someone want to buy your thing? Like you're trying to sell them. You need to be able to convince them based on what they want. Because if I'm trying to sell you something and you're like, "Dude, I don't care about that at all." Like requests per second, like so what? Like, how is that actually going to help me um you know, with the the user experience? Like that doesn't make any sense to me. And it's like, well, now if I think about that and I can go, okay, well, that's what Brian really cares about is request or sorry, is uh you know, this user experience. If I can say, hey, if we have a higher request per second, that allows these workflows to go faster and that means that these users are going to have a better experience. If I can communicate that to you, then you might be much more inclined to go, wait, tell me more about this proposal that you have. So, yeah, the the selling part and the actual format of the data. >> Yeah, 100% 100%. And like uh for one thing that I think as engineers we struggle with is we also like to be the expert. So we like to know like we we like to always have the answer. And when we feel like we don't we'll make up the answer. Um and so we can feel really uncomfortable when put in that position where I have to say hey Nick what is you know this? And it's like, well, I'm supposed to be the super smart engineer guy that I have all the answers. Um, and it's really hard for us to say something like, I don't know. I need more information in order to make that decision or or to give you guidance on it. >> And it's important that people can do that, right? I think that um you know we talk about things like psychological safety in general, but if you're in an environment where if you're like I I don't know how to say I don't know or um you know I I need time or something if you feel like you can't do that environment is probably not super stellar. But we also just have to get comfortable doing that because it's it's a lot worse to kind of masquerade as like oh I just I just know all these things and whatever. But, uh, if you truly need more time to go collect data and and be upfront and say like, "Let me let me take that away and go get it." I've seen this happen in conversations like with my CVP where like at Microsoft where people are in meetings and she'll call on them and they'll say like, "Hey, like um, great question. Like, I need to go follow up with more people on the team to go get that." And what doesn't happen is she's like, "Nope, you're fired. Get out." It's like, "Cool, thanks. Makes sense. Like, we'll follow up." Right? It's they need the data. That's fine if you don't have it right now, but that's the new task. Go take care of it. Right. And we have to be comfortable doing that. >> No, absolutely. And I think as leaders, it's important for us to recognize that and model it for our teams. Even if I have the answer, you know, if I could put together a a good uh solution on the spot, being able to model that, hey, I need more information. I need to communicate with my team. and my team seeing that uh interaction is really really valuable because for me that's how I like to establish that culture of psychological safety within the team is by being the person that doesn't know you know even though I should be the all- knowing uh just kind of where I sit in the organization. So >> but yeah I think that's a really good point right is this ability to to lead by example and to demonstrate these types of things. Um the I like what you said a little bit earlier around like you know being able to demonstrate leadership is not tied to your title, right? Leadership is is a trait. It's a set of characteristics. It's not I mean you could make up titles that have it, but that doesn't mean that you actually demonstrate leadership by having that somehow in your title. But um anyone can do it. And I think modeling behaviors is such a good way to do it because it starts off you might not feel like you're like leading by doing that necessarily. You might just say, "Okay, like I'm doing this." But what you're actually doing in some of these situations like what you were just describing is if you're demonstrating like I'm going to show people that I don't have the answer to this or that I need to follow up with this. I'm going to go do that. And you do it again and you do it again. other people see that behavior and like what you end up doing is is leading, right? You're showing people that it's okay to do that and then other people start to go, "Oh, that is that is the acceptable thing. I can follow and I can do this and and there isn't a negative consequence for doing it." And then this kind of culture emerges from that. But it is because ultimately that was a step in leadership. >> Yeah. No, 100%. Um yeah, there there's a lot that we can do for individuals on our teams to really demonstrate and lead them through that journey uh so they can start to grow those skills. >> Yeah. And would you say for like for folks that are you know interested in that path going more from an individual contributor um like they are IC's and they are trying to be you know moving up in senior taking like a leadership role um is there more beyond like okay so if they want to start bringing in things like is that is the advice that they should be more proactive about that is there an expectation where um like should they be just getting that stuff from their manager or like what does that look like in your opinion? in terms of like how they navigate that. >> I think so much of our success depends on our own ability to kind of drive things forward. Um if I'm waiting on my manager, you know, I I would still be waiting eight years for a promotion. It just it wasn't going to happen. Um and so I think it it is really important for us to take ownership and and ownership can look like hey dear manager I want to get to this level what are the steps I need to take because right our manager might be thinking about their career trajectory and their growth and not always focused on yours. So taking ownership and asking for that person and if our direct manager isn't able to do it, taking ownership and finding somebody else, you know, inside or outside the organization, there's just um but it it does require us to kind of push ourselves against that comfort zone of saying, "Hey, this is what I want." And standing behind that and finding somebody that can help uh get us there. >> Yeah, I like that a lot. I think that um as much as I would love to sit here and say, "Hey, like no, like your manager is absolutely there to support you and like they're going to help you in your growth," I'm like, I think that's what managers should be doing. And I would love to say that all of them are hyperfocused on that and they're going to do everything to help you succeed in your career. But I think the reality is like it just isn't that way in practice. As much as I would love to confidently say that, it just isn't that way. So yeah, I think I I totally agree that if you're kind of sitting back waiting, you you may more often find yourself disappointed. And >> it's that's how I look at it. There's like if you don't want to if you don't want to be as disappointed, like take initiative, try to drive, try to take action, you take ownership on these things. And at the end of the day, um, you know, if things aren't moving at the pace or in the direction you want, like you are putting in all of the time and effort to do it, you can't sit there and say like, I didn't try. So, if it's not working in your current environment and you are doing all these things, maybe that is a sign that maybe that environment is not quite the right place. And it doesn't, you know, it could be timing, could be a bunch of different factors, but if you're not doing anything and you're just waiting, like you're kind of leaving a lot on someone else for your success. And I feel like that's kind of like a not a good recipe for um for happiness. >> Yeah. No, 100%. Absolutely. And so I guess another topic that's kind of interesting is you like you said earlier, everyone's favorite two-letter word has uh introduced a lot of uncertainty for folks. Um, and I I'm curious like when we talk about AI in general, do you like do you see this being something that's uh more affecting people that are trying to get into the industry, junior, more senior? Like where do you see that having the most uncertainty for people or is it evenly spread? >> I I I think it's evenly spread but it looks different at different levels. Uh so right unfortunately we're seeing a lot of junior roles just they're they aren't open. Uh teams are saying oh well let me bring in a really strong senior and a bunch of AI tools and now we can 10x our output. Um and I don't need the juniors to do those things. Um and so I think unfortunately a lot of the folks that have gone through and gotten the CS degree or gone through the boot camps and are trying to find work are just really really struggling. um because of how organizations are kind of structuring their hiring. Um now some organizations have you know uh continued to hire junior engineers and what I find is they tend to be more uh apt to adopt some of these tools and play around with them right because they still you know at that point in our careers you know at least for me man I was super cur I was playing with everything it didn't matter what it was I was going to install it and play with it and you know um and I think many people will do that the further you progress in your career the more comfortable you get these are the technologies, this is the stack, you know, this is the architecture. I know that's what I'm sticking with. Um, I think what I'm seeing is, you know, so so juniors are struggling to to find roles, but they tend to be more apt to to adopt the tools. Seniors tend to push off the tools. You know, they're the ones that are saying, "Oh, it's just AI slop. We're going to have to rewrite this thing. It won't scale." Um, and I think a lot of that I see as fear of, well, you know, this thing is going to start to take my job. Um, you know, and I just I don't think it's going to happen. I don't see it. Uh, I think more organizations want to be able to write more highquality software and if we could do that faster and and better and, you know, all of those things, then I we can let's do it. Let's leverage some of these tools. Um, and I have seen a little bit of a shift in, you know, maybe recent weeks and months in the industry about how we're seeing it's like, okay, well, let's start to really look at it. Oh, it turns out it's just a tool. It's just another portion of the stack. Um, how can I leverage it going forward? Uh, so let me let me spend some time. Let me dig into it. Um but I do find that um not all engineers are really like eager to go and learn these tools and play around with them. Um so it's more not like a mandate from top down but almost like what I try and do is demonstrate with my team like hey this is what I'm doing. This is how I'm using it and playing with it um to kind of bring my teams along uh in adopting it. But yeah, it's it's really really interesting. Uh right now >> I like that that very last point on um like a mandate versus a demonstration. And personally, uh, I would I I really like the idea of demonstrating better than mandating because I think that when any type of mandate, and this doesn't just apply to AI, I'm thinking about scenarios where I'm sure a lot of people can relate to this, new manager comes in, new director, new VP, whatever. Someone comes in and even if their idea is great, doesn't matter if it's great or not, but if they have an idea and they're like, "We're just going to start doing this." What happens is people resist it. Doesn't, like I said, doesn't matter if it's a good idea or not. People are like, "That's just different. Uh, we don't like it." And if it's, especially if it's a bad idea, then there's even less trust. Like everything just kind of is not not in a good spot. And >> in my experience, any type of like sort of mandate is is resisted and I feel like is not as effective as what you're actually trying to accomplish. And if you're able to demonstrate and say hey look like we believe just in this example for AI like we believe that AI will help enable people we believe it will help make you more productive or avoid this class of problem whatever it is if you believe that like if you demonstrate that to people and they go oh yeah like I can see that if you're trying to demonstrate it and that's not conveying or like messaging or you know coming clear to people then maybe your demonstration sucks or maybe you're wrong like and So instead of mandating it and forcing people into it, like I think sort of it goes back to like leading, right? Like show people like, hey, this is what we could do, not you must go do this because I just feel like that is going to create friction. And um I think a lot of people see that as like you're telling me to like to go solve a problem that I don't even think exists. And that's like a very frustrating experience where you're like, well, now I'm really wasting time on whatever this silly idea is. But is that is that kind of how you see that as well or different thoughts on there? >> Uh, it is it is how I see it. Um, now one thing that kind of back to some of our earlier points around like selling and speaking to your audience, right? I'm speaking to a group of engineers. And so when I look back it's like okay well what are the things that engineers always want to do but never have time to do right writing tests writing documentation right I don't want to write the boilerplate I want to think about the architecture like now if we invest the time to understand the tools like those AI tools can do that boring stuff that we know we need that always gets pushed off right and we we'll do it you know and we never do um >> until the systems is about to fall apart. It's like, okay, I guess I have to do this now. >> Exactly. Um, but now I can be like, hey, now we get to do those things. So that as engineers, we get to do the engineering thing. We get to solve the problems. We get to think about architecture more broadly and we're not writing boilerplate anymore. Um, we're not writing those tests that we know we need but we don't have time for. Um, and so like that's one way I've really tried to sell is to speak to the engineer like those are your desires. Engineers want stable systems. They want to be able to sleep at night. Um, they want to, you know, bring on an engineer new to the team and be like, "Hey man, look at this." Like be proud of it, not like, you know, don't don't look over there. Um and yeah, so I I kind of like to use that same approach in selling to my engineers um in that way. >> That makes sense. I I like that. I think um you know, in my own I don't program at work anymore. Um just like at at Microsoft, it's been more like leading and managing teams, not actually writing code. But I write code every day outside of work. And with um with AI tools like the you know the paying down the tech debt or like refactoring things I find the best part about that is like I think a lot of developers can relate to this like we want to go clean up the code. We want to refactor things. wanted to >> and you do it and then like as soon as it's done you're like yeah but it could be even better like um and it's this never ending thing and probably a lot of people have experienced this where if you you know have you know difficulties communicating to whether it's your product manager, project manager, engineering manager, someone who is helping prioritize things and you're like we need to do this tech debt and they're like we got to do these features and you seem like you can never get that stuff prioritized. It's probably going back to like how to sell effectively in these types of conversations. But what's really cool is that you can say, "Cool, if I'm going to go fire this off to like some AI agent to go carry out the work, in my personal experience, I still get to sit down and be like, cool, this is what I want it to look like." You know, I'm having the creative conversation with either myself or some some teammates saying, "This is what we want it to go look like." But I don't really ne necessarily enjoy the point in refactoring or rewriting parts of systems where I'm like cool only 700 compilation errors left like let me go keep you know updating these things. Like that's not the fun part. The fun part is like what is this cool idea and the part in the middle sucks and then the end is like hell yeah it worked. And now with AI at least I can go fire that stuff off and watch it chip away at it. It's not perfect, but like it's doing it and I can go jump in as needed. But that's been helpful. >> No, absolutely. Um, and you know, for those of us that have spent years in the trenches and, you know, days working it out bash scripts and stitching together Stack Overflow articles to try and make this thing work. like it's kind of bananas what I can do for $158 of credits and you know just letting it run for a little while. Um the scripts and the the helper functions and all of these things that it's able to generate for us so quickly that you know it would have taken days before you know and you know back in the day you know it's just it's kind of wild to see man. Yeah, it's it's pretty incredible. And I think that you you kind of touched on this a little bit, but people like wanting to resist the technology. And I I find myself going through like phases of this, right? Like I don't I don't personally don't think AI is going away. Like I think we're probably in some type of bubble on the uh economics of it and >> all that. But um in terms of a bubble and like the technology goes away, I don't think so. Uh I think it's here to stay. I think it's going to keep growing. And I need to constantly remind myself like play with the tools. like try the things out. You know, for example, I use Visual Studio a lot as a C developer. So, I love using Copilot in Visual Studio. Okay. Does that mean that I should never use Claude or I should never use Cursor or whatever else? Like, nope. I'm trying to make myself go try those tools out. I'm trying to see like as I'm prompting and having these agents navigate situations, I'm like, "Wow, it really sucks at this." or does it like am am I the one who sucks at this and I don't understand the tooling well enough and I'm just kind of forcing myself to find this balance of don't get so stuck like if it's not doing what you need and you need to make progress go figure out how to make progress but don't give up on it don't write it off and say you know what co-pilot couldn't do that like I'm never using co-pilot again is dumb like nope like kind of rethink through how I'm going to approach it I'm starting to realize more now. Um, I feel like regardless of some of my prompts, instruction files, custom agents, I'm like, I actually need to go write what I'm like, uh, in C, we have analyzers and we can go write custom rules. And I'm like, if I write these custom rules, the code won't even build if the agent is doing the wrong thing. Maybe that's going to help give it really good guard rails. Maybe that's my next unlock. So, I'm just trying to explore and make sure that I'm not like getting stuck and being like, "This stuff sucks. I'm going to go code it all myself again." >> Yeah. Yeah. And it's tough, especially when we have, you know, a few years of experience. Like, we enjoy that building, that craftsmanship of of it. Um, and that doesn't have to go away, but you know, some of the other tasks that we don't like but do need to get done in order for it to be a stable system, hand those off and and really try it. Um, but I think I don't know it for me, I got into technology and have stayed in technology for so long because it satisfies that curiosity like there's always something new to learn. uh whether it you know it's a new cloud ecosystem or architecture or technology or you know framework or whatever it is like there's just so much that we can play with now and with you know with all the different AI tools that are coming out it it's it's it's fun again for me uh to play around with a lot of this stuff where for a while you know it's like cool another crud application you know I'm good um >> yeah another another way to do the same thing. Uh, yay. But now it's Yeah, it feels like there's a lot that's kind of booming that that feels very new again. Um, with that said, how about for for juniors, right? Um, for people that are getting into software development, I'm curious your thoughts. They're they see all these AI tools around them. They see that everyone's using it. They're kind I'm assuming most people are probably going, "Oh crap, I I really have to make sure that I'm I'm using AI for everything because this is the way of the future." How do you feel about that sort of affecting or or like positive or negative their sort of learning and kind of getting started in software development? >> Man, that's a really really good question because I think there's a lot of things that you know kind of like back to something I mentioned earlier on like there's some things you just have to learn and you can't learn it through a book. You just have to learn it hands-on. Um, and yeah, I I do worry about just, you know, handing it off to the AI and letting it do. Um, because I do think that there still needs to be some sense of like I'm going to build this thing by hand. I'm going to, you know, stand up this database. I'm going to, you know, whatever it may be. Um, I think there still needs to be some sense of that. um you know and maybe doing it the hard way, right, the old school way first and then bring in AI and see how it can enhance and improve um you know continuing to study other uh architectures and you know how did Spotify scale or you know how did Uber you know what does their system design look like. I think those areas are still really important uh for you know juniors to kind of dive into and understand. um you know the same when a lot of the the front-end frameworks really came out is like doesn't like not every organization is going to use Angular or React um learn the underlying technologies learn the HTML and the CSS and when you understand that then you can easily translate it to another language similar with any other you know kind of runtime language um yeah just just I think it's just spending time exploring playing um I think that's how most of us learn best, especially in this kind of tech world. >> I I completely agree with that. The this idea of like like if you if you don't have any of the hands-on part, I feel like that's going to, you know, dramatically inhibit your like rate of learning or like effectiveness of learning. I guess the I'm just going to throw this out there because I don't necessarily believe it, but I'm trying to I'm I'm curious if this is how it pans out. I'm curious if there's enough people out there getting into software development that are just like AI first, AI, like kind of like they start legitimately pure vibe coding. Like they don't actually know what's going on. And I don't mean that in a condescending way. I just mean like legitimately they're brand new to it. >> Code came out. Cool. Copy paste. And they keep doing this. >> Is there like a wave of developers that come through? That's the only way they've learned, but they're so effective at it that they learn through these AI tools and they're just so good at using AI that it actually doesn't matter that they didn't have some of those fundamentals. Like I said, I don't necessarily believe it, but I'm curious to see if there's something like that that pans out. >> I I think so. Um, and right, history doesn't repeat itself. uh but it looks very similar you know however that you know I'm misquing um I think we had similar scenarios you know with folks that you know had other took other approaches to learning software engineering 10 years ago. Um and you know the way they approached is like well does it work? Does it show up like yes there it might be littered with security vulnerabilities but you know it it works and so I'm going to keep progressing on. Um, I don't I think we're just doing the same thing that we were doing before, just faster. Uh, you know, vibe coding and all of that is just a new term for what we've experienced throughout the industry. Um, you know, at least as long as I've been in it. >> Yeah. like this this again this curiosity of mine is kind of like to use an example um you know you're you're building something and along the way like sure because you didn't have some of the fundamental understanding of things there's lots of issues and you might not run into them until later but then you do run into them you did you had security faults or like you had scaling issues because you actually built something that needed to start scaling up and like is the answer well I guess at that point everything falls apart and that's the end software development for you or is it well the thing I know how to use is my set of AI tools. Okay, AI tools I have this problem I'm very good at using you help and I'm I'm just curious if that's a path that people take and it ends up working like it's not my path and I can't I don't see that working for me but I'm just curious if that's how it pans out. Yeah, it'll be interesting to see I think over the next couple years, you know, like what software does, you know, how does that shift or do we get into a place where we just have very small bespoke applications, you know, that a small group of individuals are using versus these large behemoth application? Like, you know, how does that play out? um you know where scaling and security aren't as important um when it's just a very small you know thing. >> Yeah. Exactly. And I I guess one one final question I have for you and you touched on it a little bit. You said that from your perspective you don't see like you know AI replacing software engineers and like sort of uh I assume that means that you you see the role existing for for time to come. Um yeah, like in from your perspective, do you see that being an opportunity for more roles? Is it um like different types of roles, capacity for software engineers like in in sort of the job market? I'm curious uh if you have any more thoughts on on what AI looks like in terms of affecting like software engineering roles in general. Uh I I do think we're going to still can see still see continued growth in software engineering uh more roles. I my crystal ball tells me unfortunately most people are going to be looking for senior developers who can kind of guide these build these agents. Um you know so I think there's going to be a strong need for mentorship. uh if you know there is a junior that is able to join an organization really really mentor them kind of teach them the ropes um and I yeah I think it's just we're going to be building a lot more software it's going to look a little bit different you know as far as the size and the scale and our customer base um you know I think we're going to you know some of the things that I'm seeing is like I can vibe code a fairly working solution where it used to be a series of like you know wireframes and then like Figma type of document and that sort of thing like I think we're going to get we're going to start with like some sort of almost working application and then we're going to to enhance uh from there. So I think some of the skills that I want to really focus on is how can I take those you know those vibecoded applications and start to productionalize them. How do I identify the areas where uh you know there could be issues? Um, you know, for me, I've always focused on simplifying. So, how can I make things even more simple so that we can uh build more? >> Yeah. And that's a Thank you. I think that's a I think that's interesting where like vibecoded things uh are are truly kind of getting us to like a a prototype instead of like having just a mockup. It's like you can actually click around in this thing. Is it going to be perfect? No. No. But like you can you can click around and you can actually start to feel like you are using something and obviously this depends on the type of software that's being built or if I'm right now I'm referring to something with a user interface but you could have a mockup of you know some type of backend thing running and I mean you might not have to have you know your your database like your your system published running in the cloud scaled out but you could have something where you have you know the logic is doing something you have uh stubbed out resources and whatever and you can be like, "Hey, like this is actually viable to go do something, but we're we're at this point where we can use AI to get us there pretty quick." And to your point, cool. Now that we start to see some of that, that's interesting because there's with prototypes in general, there's lots of just throwaway. Most things we prototype, we toss them out. And now that we can do that pretty quick and have probably what feels like a better um feel for like this prototype versus just like a mockup >> like now we can do that faster. How do we start taking those things? Like is there a more effective way to say like do we take the prototype and go build on that or do we say great the prototype's awesome still toss it but now we know like cool let's go start from scratch and build out that thing that the prototype proved like was working. But I I think there's going to be personally a lot more of that where um how do we go prototype to like to production whether that's building on it or starting it again from scratch but using the same idea. So um I think it'll be very interesting. >> Yeah. >> Cool. Well, Brian, thank you so much for making the time to chat with me. Um for folks that want to get in touch with you, what is the best way for them to reach out and see what you're up to? Yeah, I would encourage folks to just find me online. Brianchildress.co is my website. From there, it'll kind of spider out into, you know, different social media or send me an email. Happy to connect. I love working with engineers at different levels, uh, different phases of their journey, uh, and helping them out. Um, you know, I didn't have a traditional path to get here and I know a lot of others don't either. Um, so I'd love to to support, you know, folks in any way that I can. Awesome. Well, thanks again. I do really appreciate it and I think that there's a lot of uh interesting takeaways for folks that were watching. So, thanks again. >> Thanks for the opportunity.

Frequently Asked Questions

What was Brian's career path before entering the tech industry?

I started my career in outdoor recreation, guiding activities like whitewater rafting and rock climbing. I didn't have a passion for computers until I went back to graduate school for geographic information systems, where I discovered my interest in software development.

How did Brian deal with imposter syndrome during his transition into tech?

Imposter syndrome was a significant challenge for me. I didn't have a formal software engineering background, which made me feel unworthy at times. I overcame it by dedicating a lot of time to learning on the job, seeking mentorship, and immersing myself in the tech community.

What advice does Brian give for those looking to transition from individual contributor roles to leadership positions?

I believe that leadership opportunities exist at all levels, not just in formal titles. It's important to take ownership of your career, seek out leadership roles in projects, and communicate your goals with your manager. Building relationships and understanding the needs of your team can also help you grow into a leadership role.

These FAQs were generated by AI from the video transcript.
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